Why I Choose to Work With Founders in Transition

Several years ago, I found myself on a Zoom call with the global head of HR at the holding company that had acquired our agency a few years earlier. It was a routine conversation at first—updates, leadership priorities, the usual back-and-forth.

Then she paused, looked at me through the screen, and asked a question I wasn’t prepared for:

“What do you think you want to do next—when you someday leave your role as CEO?”

I’d been leading agencies in one form or another for nearly three decades. My career had always been about the next client pitch, the next hire, the next quarter, the next move for the business. But I’d never really stopped to ask what I wanted next—beyond the business.

And in that moment, it hit me: I didn’t have an answer.

The question lingered long after the call ended. It rattled around in my head for months, surfacing in quiet moments I would have rather ignored. The truth was, I had no vision, no plan, and no clear sense of who I might be if the role I’d carried for so long was no longer mine. That realization was terrifying.

A few years later, the holding company made a strategic decision to merge our Cincinnati agency with a sister shop. Suddenly, the “someday” my HR colleague had asked about wasn’t theoretical anymore. It was here.

It was time for me to move on.

But move on to what?

For years, a close friend had been nudging me to think about life beyond the agency. And yet, I had avoided doing the hard work. I hadn’t created a vision that pulled me forward. Nothing with substance. Nothing that gave me confidence.

From the outside, it looked like I had options. From the inside, I felt completely unprepared.

Why This Matters

That experience showed me how unprepared many business owners are—not just for the transaction itself, but for the shift in identity that follows. Transition isn’t only about leaving behind a company. It’s about evolving beyond the business identity you’ve carried for decades.

Looking back, I can see where the gaps were.

• I hadn’t separated my identity from my role.

• I didn’t have a compelling vision for what was next.

• I struggled with issues of control and trust—how to let go of what I’d built.

• I wasn’t sure how to talk with my family, or even myself, about the changes ahead—those critical conversations and relationships that shape transition.

• My capacity was maxed out; I was running so hard in the business that I had no margin to plan beyond it.

• And while the company was financially sound, my own readiness for the business to transition wasn’t there.

I’ve seen and felt parts of what comes with building and leading a business: the intensity, the sacrifice, the satisfaction of creating something that lasts—and the weight of carrying it all. And I’ve also seen what happens when that weight suddenly lifts, when the role ends, and you’re left wondering what’s next.

That’s why this work matters to me now. I don’t want other business owners to experience transition the way I did—uncertain, reactive, and without a clear picture of what lies ahead.

A successful exit is only part of the story. What matters just as much is creating a transition that opens space for a future that feels purposeful—for you, your family, and the people who’ve built alongside you.

The Founder’s Transition Lab

That’s why I helped create The Founder’s Transition Lab (FTL).

The Lab isn’t about running a better business. It’s about preparing for what happens after. It’s about giving business owners a trusted space to step back, reflect, and design the future they actually want.

In the Lab we focus on three things:

• Clarity: Getting honest about what you really want—not just what others expect.

• Confidence: Building the mindset and capacity to let go of the business without losing yourself.

• Connection: Doing this work alongside a small group of peers who understand the complexity and can walk with you through it.

We do this through small, curated cohorts, one-on-one coaching, and a structured framework that helps business owners move from uncertainty to a clear, confident plan for the future.

Beyond the Numbers

At the end of the day, selling your business is more than a financial transaction. It touches everything—your identity, your relationships, your sense of purpose.

When I went through my own exit, I realized how little space there was to process those things. Most of the focus was on the financials and deal terms. But the harder work was figuring out who I was becoming, and how to move forward in a way that felt true.

That’s what The Founder’s Transition Lab is here to offer. It’s not about leaving behind everything you’ve built—it’s about creating the space and support to evolve beyond your business identity and carry the best of yourself into what’s next.

Because the truth is, this work takes time. It can’t be rushed in the months leading up to a deal. It takes 12–24 months of intentional work to do it right.

So if you’re even beginning to think about stepping away in the next decade, now is the time to start.

Not just to exit well—but to step into what’s next with clarity, confidence, and purpose.

Because the real goal isn’t simply to leave the business. The real goal is to step into a life you’re excited to live.